Discover winter rentals Dutchess County - We found 469 exact matches
About Dutchess County Winter Rental on Vacation Cottage
At Vacation Cottage, we showcase a diverse array of accommodations in Dutchess County, NY perfect for your winter retreat or seasonal escape. Our listings encompass hotels, private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments, ensuring travelers find their ideal accommodation. Vacation Cottage's winter vacation homes boast premier amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
Whether you're seeking to escape the snow or embrace it, Vacation Cottage facilitates your connection to the finest cabins, bungalows, lodges, rent-by-owner homes, and the best accommodations in both sunny retreats and ski resorts. Vacation Cottage ensures your winter getaway becomes an unforgettable experience.
Vacation Cottage presents luxury options for travelers seeking to rent a place in Dutchess County. To access these benefits and book your winter vacation home, simply utilize the Vacation Cottage filter option. Enter your travel dates, refine your search with filters for property type and amenities, then choose from our extensive list of exceptional winter vacation rentals hassle-free. Our interactive map further enhances your experience, allowing you to explore destinations worldwide or within Dutchess County and unlock incredible deals. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Dutchess County Winter Rentals
What are the top rated Winter Rentals in Dutchess County?
There are a lot of options in Dutchess County. If you plan on staying in the Dutchess County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Dutchess County:
- Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
- WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
- Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
- Quiet Lakefront Retreat only 80 minutes from NYC- with Private Dock
- Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
- Charming Brick House -Hudson Valley
- PRIVATE 65 ACRE ESTATE - POOL, TENNIS, PICKLEBALL, 4BRnBOOK JULY OR AUG 2026 NOW
- Peaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit
- Hudson Valley Horse Farm Retreat in Salt Point
- The Beech House - Light, Open, Stunning Views, in the heart of the Hudson Valley
How much does it cost to rent a place to stay near Dutchess County in the wintertime?
The average cost for winter rentals in Dutchess County is $636 per night. Vacation Cottage has a wide list of great winter places to stay near Dutchess County that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Dutchess County that allow pets?
Yes, here are the top cottage/chalet rentals in Dutchess County that allow you to bring your pet or dog:
- rural, serene + sophisticated space
- Modern NY Home with Views By Hudson Valley Hiking!
- Spacious New 5-bedroom holiday house in lovely Hudson Valley
- the suite @ barn & bike - private, bucolic, serene setting
See all pet-friendly vacation rentals in Dutchess County on Vacation Cottage
Do you have any winter rentals in Dutchess County that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Dutchess County to find what works for you.
Are there winter accommodations in Dutchess County that have indoor swimming pools?
As of 2025, the data from Vacation Cottage shows that there are over 469 private swimming pools or indoor pools accommodations near Dutchess County along with other great amenities.
Do any winter holiday rentals in Dutchess County have hot tubs?
About 469 holiday rentals in Dutchess County boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Dutchess County?
Yes, there are many luxury places to stay in Dutchess County for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Dutchess County with all the best amenities for your next trip.
